What is the smallest positive integer $a$ such that $a^{-1}$ is undefined $\pmod{55}$ and $a^{-1}$ is also undefined $\pmod{66}$?
Explanation: An integer $a$ has an inverse $\pmod{55}$ if and only if $\gcd(a,55)=1$. Similarly, an integer $a$ has an inverse $\pmod{66}$ if and only if $\gcd(a,66)=1$.

Since we're looking for an integer that doesn't have an inverse modulo either $55$ or $66$, we want $a$ such that $\gcd(a,55)>1$ and $\gcd(a,66)>1$. Thus $a$ must be divisible by either $5$ or $11$, and $a$ must also be divisible by either $2$, $3$, or $11$. The smallest positive integer that satisfies both properties is $\boxed{10}$.